1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues
Title | 1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues |
Publication Type | Journal Article |
Year of Publication | 2005 |
Authors | Karanjule, NS, Markad, SD, Sharma, T, Sabharwal, SG, Puranik, VG, Dhavale, DD |
Journal | Journal of Organic Chemistry |
Volume | 70 |
Issue | 4 |
Pagination | 1356-1363 |
Date Published | FEB |
Type of Article | Article |
ISSN | 0022-3263 |
Abstract | The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine 3a,b and 2-hydroxy-1-deoxy-8a-epi-castanospermine 3c,d is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol to D-glucose-derived nitrone 4, followed by tosylation, that afforded four diastereomeric sugar-substituted isoxazolidines 5a-d with the desired regioselectivity. The one-pot conversion of 5a-d to pyrrolidines 8a-d by hydrogenolysis, removal of 1,2-acetonoide functionality, and hydrogenation afforded corresponding target molecules 3a-d. |
DOI | 10.1021/jo048176x |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 4.785 |
Divison category:
Center for Material Characterization (CMC)
Physical and Materials Chemistry